Our invention relates to the tricyclic ether-substituted acetic acid having the structure: ##STR2## and microbiological processes for producing same from one or both of the compounds having the structures: ##STR3## as a substrate and using one of the microorganisms: Cryptococcus albidus, ATCC 20918
Bensingtonia ciliata, ATCC 20919 PA1 Cryptococcus laurentii, ATCC 20920 or PA1 Cryptococcus albidus, ATCC 20921.
Also described is the use of the tricyclic ether-substituted acetic acid having the structure: ##STR4## is augmenting, enhancing or imparting an aroma or taste in or to a smoking tobacco article or smoking tobacco by causing the tobacco to be richer, smoother, and have more "tobacco body".
The tricyclic ether-substituted acetic acid having the structure: ##STR5## along with the cyclic ether having the structure: ##STR6## were discovered to be produced in carrying out the fermentation process commencing with sclareol having the structures: ##STR7## in an effort to produce sclareolide having the structure ##STR8##
The pathway from sclareolyde to sclareolide was originally determined to be: ##STR9## with the ultimate end product being the compound having the structure: ##STR10## an important material for use in perfumery.
The compound having the structure: ##STR11## has been shown to be useful in U.S. Pat. No. 4,798,799 issued Jan. 17, 1989 as an intermediate in the creation of the compound having the structure: ##STR12## and has also been shown to be a useful precursor of the compound having the structure: ##STR13## at column 8, lines 58-60 of U.S. Pat. No. 4,798,799.
Indeed, U.S. Pat. No. 4,798,799 discloses the utilization of a culture containing the microorganism Hyphozyma roseoniger having the identifying characteristics of CBS 214.83 and ATCC 20624 capable of producing the diol having the structure: ##STR14## in a recoverable quantity upon the transformation of compounds including the compound having the structure: ##STR15## (sclareol). Table IV, thereof at column 12, lines 15-28 discloses yields of 96% when carrying out the reaction: ##STR16## under fermentation conditions using ATCC 20624.
There is no teaching or suggestion in the prior art of producing during the foregoing reaction sequences the tricyclic ether-substituted acetic acid having the structure: ##STR17##
Materials which are capable of causing tobacco to be richer, smoother and have more body; particularly, for the purposes of imparting, augmenting or enhancing aroma and taste in "low delivery" cigarettes where the smoke is thinner are highly desirable in the smoking tobacco art. Many of the natural materials which provide such aroma and taste nuances are high in cost, unobtainable at times, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
The tricyclic ether-substituted acetic acid having the structure: ##STR18## can be classified as a "natural product" in view of the process used in preparing it from natural sclareol having one or both of the structures: ##STR19##
Nothing in the prior art discloses the compound having the structure: ##STR20## or its use in smoking tobacco articles or smoking tobacco per se.